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Which of the following represents the energy levels of the molecular orbitals of cyclopentadienyl anion? Which of the following represents the energy levels of the molecular orbitals of cyclopentadienyl anion?   A)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

E) B) and C)
F) All of the above

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound?   A)  1-bromo-2-fluoro-4-toluene B)  4-bromo-2-fluorotoluene C)  2-bromo-4-fluorophenol D)  4-bromo-2-fluoroxylene


A) 1-bromo-2-fluoro-4-toluene
B) 4-bromo-2-fluorotoluene
C) 2-bromo-4-fluorophenol
D) 4-bromo-2-fluoroxylene

E) All of the above
F) C) and D)

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What is the intermediate in the reaction of ethylbenzene with NBS in the presence of benzoyl peroxide to give 1-bromo-1-phenylethane?


A) Benzylic anion
B) Benzylic cation
C) Benzylic radical
D) Benzylic carbene

E) A) and B)
F) A) and C)

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What is the correct assignment of the names of the following substituted benzenes? What is the correct assignment of the names of the following substituted benzenes?   A)  1 = styrene; 2 = benzaldehyde; 3 = cumene B)  1 = anisole; 2 = benzaldehyde; 3 = toluene C)  1 = styrene; 2 = xylene; 3 = toluene D)  1 = aniline; 2 = phenol; 3 = cumene


A) 1 = styrene; 2 = benzaldehyde; 3 = cumene
B) 1 = anisole; 2 = benzaldehyde; 3 = toluene
C) 1 = styrene; 2 = xylene; 3 = toluene
D) 1 = aniline; 2 = phenol; 3 = cumene

E) None of the above
F) A) and B)

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What are the relative positions of the substituents in the following structure? What are the relative positions of the substituents in the following structure?   A)  anti B)  meta C)  ortho D)  para


A) anti
B) meta
C) ortho
D) para

E) B) and D)
F) A) and B)

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What is the major organic product obtained from the following reaction? What is the major organic product obtained from the following reaction?   A)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

E) A) and B)
F) A) and C)

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Which of the following is not true about [the bridged [10]annulene shown below? Which of the following is not true about [the bridged [10]annulene shown below?   A)  all of the carbon atoms of bridged [10]annulene are all in the same plane B)  bridged [10]annulene is aromatic C)  bridged [10]annulene undergoes substitution reactions similar to benzene D)  bridged [10]annulene has 10 pi electrons


A) all of the carbon atoms of bridged [10]annulene are all in the same plane
B) bridged [10]annulene is aromatic
C) bridged [10]annulene undergoes substitution reactions similar to benzene
D) bridged [10]annulene has 10 pi electrons

E) None of the above
F) All of the above

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Which of the following is not true about [18]annulene? Which of the following is not true about [18]annulene?   A)  [18]annulene is planar B)  [18]annulene is aromatic C)  [18]annulene gives one peak in the <sup>1</sup>H NMR spectrum D)  [18]annulene has 18 pi bonds


A) [18]annulene is planar
B) [18]annulene is aromatic
C) [18]annulene gives one peak in the 1H NMR spectrum
D) [18]annulene has 18 pi bonds

E) None of the above
F) A) and B)

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What is the best choice of reagent to achieve the following reaction? What is the best choice of reagent to achieve the following reaction?   A)  Br<sub>2</sub>, CCl<sub>4</sub> B)  HBr, H<sub>2</sub>O C)  Br<sub>2</sub>, light D)  NaBr


A) Br2, CCl4
B) HBr, H2O
C) Br2, light
D) NaBr

E) C) and D)
F) B) and D)

Correct Answer

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound?   A)  2-nitro-6-carboxybromobenzene B)  2-bromo-1-nitro-4-benzoic acid C)  2-bromo-4-carboxynitrobenzene D)  3-bromo-4-nitrobenzoic acid


A) 2-nitro-6-carboxybromobenzene
B) 2-bromo-1-nitro-4-benzoic acid
C) 2-bromo-4-carboxynitrobenzene
D) 3-bromo-4-nitrobenzoic acid

E) C) and D)
F) A) and B)

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Which of the following is not true about cyclooctatetraene?


A) The planar conformation is antiaromatic
B) In the planar conformation there are two electrons in degenerate nonbonding pi orbitals.
C) In the tub conformation the pi system is not conjugated
D) The tub conformation is aromatic

E) B) and C)
F) A) and D)

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What is the correct assignment of the names of the following heterocycles? What is the correct assignment of the names of the following heterocycles?   A)  1 = pyrrole; 2 = thiophene; 3 = pyridine B)  1 = thiophene; 2 = furan; 3 = pyrrole C)  1 = furan; 2 = pyrrole; 3 = thiophene D)  1 = furan; 2 = thiophene; 3 = pyrrole


A) 1 = pyrrole; 2 = thiophene; 3 = pyridine
B) 1 = thiophene; 2 = furan; 3 = pyrrole
C) 1 = furan; 2 = pyrrole; 3 = thiophene
D) 1 = furan; 2 = thiophene; 3 = pyrrole

E) A) and C)
F) B) and C)

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Which orbital contains the lone pair on the nitrogen atom of pyridine?


A) s
B) p
C) sp
D) sp2

E) B) and C)
F) A) and B)

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What is the major organic product obtained from the following reaction? What is the major organic product obtained from the following reaction?

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How many p orbital electrons are present in furan?


A) 4
B) 6
C) 7
D) 8

E) All of the above
F) A) and D)

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What is the major organic product obtained from the following reaction? What is the major organic product obtained from the following reaction?   A)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

E) A) and B)
F) C) and D)

Correct Answer

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Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene? Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene?   A)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

E) None of the above
F) A) and D)

Correct Answer

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What is the correct assignment of the names of the following fused arenes? What is the correct assignment of the names of the following fused arenes?   A)  1 = naphthalene; 2 = anthracene; 3 = pyrene B)  1 = naphthalene; 2 = phenanthrene; 3 = coronene C)  1 = naphthalene; 2 = anthracene; 3 = benzo[a]pyrene D)  1 = anthracene; 2 = naphthalene; 3 = coronene


A) 1 = naphthalene; 2 = anthracene; 3 = pyrene
B) 1 = naphthalene; 2 = phenanthrene; 3 = coronene
C) 1 = naphthalene; 2 = anthracene; 3 = benzo[a]pyrene
D) 1 = anthracene; 2 = naphthalene; 3 = coronene

E) A) and D)
F) A) and C)

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Which of the following heterocycles is not aromatic? Which of the following heterocycles is not aromatic?   A)  1 B)  2 C)  3 D)  4


A) 1
B) 2
C) 3
D) 4

E) B) and D)
F) All of the above

Correct Answer

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List all of the requirements of a molecule for it to be considered aromatic.

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An aromatic molecule has an un...

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